The reaction of aromatic amines with benzyltrimethylammonium dichloroiodate(1—) in dichloromethane–methanol in the presence of calcium carbonate powder for several hours at room temperature gave selectively iodosubstituted aromatic amines in good yields.
The reaction of phenols with benzyltrimethylammonium dichloroiodate(1–) in dichloromethane-methanol in the presence of CaCO3 or NaHCO3 for several hours at room temperature gave iodophenols in good yields.
The reaction of acetanilides with tetraalkylammonium polyhalides, such as tetrabutylammonium tribromide, benzyltrimethylammonium tribromide, and benzyltrimethylammonium chlorobromate(1–), in dichloromethane-methanol at room temperature gave bromosubstituted acetanilides in good yields, respectively.
Reaction of primary alcohols or simple ethers, α,ω-diols or cyclic ethers, and secondary alcohols with sodium bromate in the presence of catalytic amount of hydrobromic acid under mild conditions gave dimeric esters, lactones, and ketones in fairly good yields, respectively.
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